#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/14/2201476.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2201476
loop_
_publ_author_name
'Benali-Cherif, Nourredine'
'Benguedouar, Lamia'
'Cherouana, Aouatef'
'Bendjeddou, Lamia'
'Merazig, Hocine'
_publ_section_title
;
 <small>L</small>-Histidinium dinitrate
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o822
_journal_page_last               o824
_journal_paper_doi               10.1107/S1600536802011625
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C6 H11 N3 O2 2+, 2N O3 1-'
_chemical_formula_moiety         'C6 H11 N3 O2 2+, 2N O3 1-'
_chemical_formula_structural     'C6 H11 N5 O8'
_chemical_formula_sum            'C6 H11 N5 O8'
_chemical_formula_weight         281.20
_chemical_name_common            'L-histidinium binitrate'
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00(2)
_cell_angle_beta                 90.000(10)
_cell_angle_gamma                90.000(10)
_cell_formula_units_Z            4
_cell_length_a                   5.4810(2)
_cell_length_b                   8.2860(5)
_cell_length_c                   25.53500(10)
_cell_measurement_reflns_used    8658
_cell_measurement_temperature    293
_cell_measurement_theta_max      26.35
_cell_measurement_theta_min      1.59
_cell_volume                     1159.69(8)
_computing_cell_refinement
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'KappaCCD Reference Manual (Nonius, 1998)'
_computing_data_reduction        'DENZO and SCALEPACK'
_computing_molecular_graphics
'Raster3D (Merritt et al., 1997) and PLUTON (Spek, 1990)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.911
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_method       φ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_av_sigmaI/netI    0.0628
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            8658
_diffrn_reflns_theta_full        26.35
_diffrn_reflns_theta_max         26.35
_diffrn_reflns_theta_min         1.59
_diffrn_standards_decay_%        <0.1
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             584.39
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.136
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         1286
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0331P)²+0.3591P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0905
_reflns_number_gt                1186
_reflns_number_total             1286
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            dn6035.cif
_cod_data_source_block           I
_cod_database_code               2201476
_cod_database_fobs_code          2201476
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C1 0.1369(5) 0.2147(3) 0.06582(10) 0.0413(6) Uani d . 1 . . C
C2 0.2991(5) 0.3515(3) 0.08398(9) 0.0367(5) Uani d . 1 . . C
H2 0.4687 0.3141 0.0847 0.044 Uiso calc R 1 . . H
C3 0.2266(5) 0.4075(3) 0.13888(9) 0.0441(6) Uani d . 1 . . C
H3 0.0568 0.4405 0.1383 0.053 Uiso calc R 1 . . H
H3' 0.2403 0.3169 0.1627 0.053 Uiso calc R 1 . . H
C4 0.3760(5) 0.5431(3) 0.15945(8) 0.0371(5) Uani d . 1 . . C
C6 0.6786(6) 0.6688(3) 0.19920(10) 0.0514(7) Uani d . 1 . . C
H6 0.8198 0.6887 0.2183 0.062 Uiso calc R 1 . . H
C5 0.3488(6) 0.7038(3) 0.15433(10) 0.0477(6) Uani d . 1 . . C
H5 0.2214 0.7556 0.1371 0.057 Uiso calc R 1 . . H
N1 0.2764(4) 0.4850(2) 0.04518(7) 0.0397(5) Uani d . 1 . . N
H3N1 0.3032 0.4467 0.0131 0.060 Uiso calc R 1 . . H
H2N1 0.3856 0.5613 0.0524 0.060 Uiso calc R 1 . . H
H1N1 0.1270 0.5267 0.0468 0.060 Uiso calc R 1 . . H
N2 0.5858(4) 0.5227(3) 0.18842(7) 0.0438(5) Uani d . 1 . . N
H1N2 0.6469 0.4317 0.1980 0.053 Uiso calc R 1 . . H
N3 0.5389(5) 0.7774(3) 0.17855(9) 0.0550(7) Uani d . 1 . . N
H1N3 0.5628 0.8799 0.1800 0.066 Uiso calc R 1 . . H
N4 0.7818(4) 0.7487(3) 0.05698(8) 0.0431(5) Uani d . 1 . . N
N5 0.7913(5) 0.1268(3) 0.20650(9) 0.0509(6) Uani d . 1 . . N
O1 0.1698(6) 0.0859(2) 0.09366(10) 0.0888(10) Uani d . 1 . . O
H1 0.0791 0.0141 0.0832 0.133 Uiso calc R 1 . . H
O2 -0.0073(4) 0.2273(2) 0.03089(7) 0.0536(5) Uani d . 1 . . O
O3 0.7709(4) 0.5988(2) 0.06161(8) 0.0580(5) Uani d . 1 . . O
O4 0.5985(5) 0.8287(3) 0.04941(9) 0.0765(8) Uani d . 1 . . O
O5 0.9865(4) 0.8132(3) 0.05967(10) 0.0684(7) Uani d . 1 . . O
O6 0.6101(5) 0.1164(3) 0.17807(11) 0.0849(9) Uani d . 1 . . O
O7 0.8534(4) 0.2613(2) 0.22367(8) 0.0578(6) Uani d . 1 . . O
O8 0.9039(5) 0.0055(3) 0.21913(11) 0.0886(9) Uani d . 1 . . O
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 C1 O1 125.0(2)
O2 C1 C2 123.4(2)
O1 C1 C2 111.5(2)
N1 C2 C1 107.67(18)
N1 C2 C3 111.25(19)
C1 C2 C3 110.8(2)
C4 C3 C2 114.2(2)
C5 C4 N2 105.4(2)
C5 C4 C3 130.7(3)
N2 C4 C3 123.8(2)
N3 C6 N2 108.6(2)
C4 C5 N3 108.4(3)
C6 N2 C4 108.4(2)
C6 N3 C5 109.1(2)
O4 N4 O5 121.2(2)
O4 N4 O3 121.1(3)
O5 N4 O3 117.7(2)
O8 N5 O6 120.3(2)
O8 N5 O7 120.3(2)
O6 N5 O7 119.3(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O2 . 1.196(3) ?
C1 O1 . 1.295(3) ?
C1 C2 . 1.513(3) ?
C2 N1 . 1.490(3) ?
C2 C3 . 1.529(3) ?
C3 C4 . 1.486(3) ?
C4 C5 . 1.346(3) ?
C4 N2 . 1.378(3) ?
C6 N3 . 1.294(4) ?
C6 N2 . 1.342(3) ?
C5 N3 . 1.356(4) ?
N4 O4 . 1.219(3) ?
N4 O5 . 1.244(3) ?
N4 O3 . 1.249(3) ?
N5 O8 . 1.223(3) ?
N5 O6 . 1.233(3) ?
N5 O7 . 1.245(3) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H3N1 O2 3 0.89 2.10 2.876(3) 144.8
N1 H2N1 O3 . 0.89 2.15 2.900(3) 141.9
N1 H2N1 O4 . 0.89 2.51 3.352(4) 159.2
N1 H2N1 N4 . 0.89 2.67 3.541(3) 165.6
N1 H1N1 O3 1_455 0.89 2.08 2.957(3) 170.3
N1 H1N1 O5 1_455 0.89 2.52 3.171(3) 130.8
N1 H1N1 N4 1_455 0.89 2.65 3.495(3) 158.5
N2 H1N2 O7 . 0.86 1.93 2.767(3) 165.6
N2 H1N2 N5 . 0.86 2.66 3.499(3) 166.6
N3 H1N3 O6 1_565 0.86 1.98 2.836(3) 176.0
N3 H1N3 O8 1_565 0.86 2.36 2.940(3) 125.0
N3 H1N3 N5 1_565 0.86 2.49 3.287(3) 153.9
O1 H1 O5 1_445 0.82 1.84 2.621(3) 158.3
